N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine
[CAS# 81265-93-2]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Deoxynucleotides and their analogues
• Name: N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine
• Synonyms: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxyoxolan-2-yl]purin-6-yl]benzamide
• Molecular Formula: C₄₄H₄₉N₅O₇Si
• Molecular Weight: 787.97
• CAS Registry Number: 81265-93-2
• SMILES: CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)COC(C5=CC=CC=C5)(C6=CC=C(C=C6)OC)C7=CC=C(C=C7)OC)O

Properties

• Solubility: Insoluble (1.1E^-6 g/L) (25 °C), Calc.^*
• Density: 1.23±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P280-P305+P351+P338

Discovery and Applications

N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine (Bz-dmt-TBDMS-Ado) is a modified nucleoside derived from adenosine. It has attracted great attention in the fields of biochemistry and molecular biology due to its unique properties and applications in nucleic acid synthesis and modification.

The discovery of Bz-dmt-TBDMS-Ado stems from the development of stable and versatile nucleoside analogs for synthetic biology. Traditional nucleosides usually have limited stability and reactivity, which hinders their use in complex biochemical processes. The introduction of protecting groups such as benzoyl (Bz), dimethoxytrityl (DMT), and tert-butyldimethylsilyl (TBDMS) addresses these limitations and enhances the stability and reactivity of nucleosides.

Bz-dmt-TBDMS-Ado has three main modifications: N6-benzoyl protects the amine group on adenine to prevent unwanted reactions; 5'-O-(4,4'-dimethoxytrityl) protects the 5'-hydroxyl to facilitate sequential nucleoside addition in oligonucleotide synthesis; and 2'-O-(tert-butyldimethylsilyl) protects the 2'-hydroxyl to improve stability and selectivity during synthesis.

Bz-dmt-TBDMS-Ado is widely used in solid-phase oligonucleotide synthesis. Its protecting groups prevent premature reactions, allowing sequential addition of nucleosides to form precise DNA or RNA sequences.

The compound facilitates the creation of modified nucleic acids with enhanced properties, such as increased resistance to nuclease degradation, increased binding affinity, and improved pharmacokinetic profiles. These modified nucleic acids are essential for the development of therapeutic oligonucleotides, such as antisense oligonucleotides and small interfering RNA (siRNA).

Bz-dmt-TBDMS-Ado is fundamental for studying nucleic acid interactions, enzyme mechanisms, and developing new biotechnology tools. Its stability and versatility make it an essential component in the synthesis of labeled or chemically modified nucleic acids for research and diagnostic applications.

References

1997. The solid-phase synthesis of 2'-5'-linked oligoriboadenylates containing 8-bromoadenine. Applied Biochemistry and Biotechnology, 62(2-3).
DOI: 10.1007/bf02787839